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Investment manager Kristy Junco views clothing as an investment. So when she fell in love with a pair of Chloe boots at Tootsies, she justified the price because she knew "they'll be good for many seasons." She can wear them with a dress to lend an edgy touch to a classic look or, as she did here, pair them with casual jeans, a black top from Banana Republic, a Missoni cardigan that she bought on sale online and a chain necklace she purchased at Muse. "It's a combination of silver and gold, so it goes with everything," she said. Like a lot of women, Junco mixes "high/low" pieces. "I can't tell you how many times the most expensive thing I'm wearing is my handbag or my shoes," she said.